For more – and far better – allegories and imaginative contemplations of reality, I recommend these wonderful resources. I am including links for your convenience, but if you find one no longer works, simply search Christianbook.com, Amazon, or your local bookseller.
Allegories
The Pilgrim's Progress
This prince of allegories was penned by John Bunyan in 1678 while he was imprisoned for preaching the Gospel without authorization by the official Church of England. It is the world's second best-selling book after the Bible. It has had a deep impact on both my soul and my interest in the genre. I personally love the antique language, but if you don't care for thees and thous, there is a modern-language version available. In addition you can find DVDs, children's versions and many other works based on Bunyan's classic.
The Pilgrim's Progress (classic version)
The Pilgrim's Progress (modern language version)
Hinds' Feet on High Places
by Hannah Hurnard
In this beautiful allegory that helps us grow in trust and maturity, you'll meet the young woman Much-Afraid as she follows the Shepherd through difficulties to the high places, accompanied by her companions, Sorrow and Suffering. An allegory in very traditional style.
Mountains of Spices (another allegory by Hannah Hurnard)
The Furniture of Heaven
by Mike Mason
A collection of short allegories that cover a vast range of styles and subject matter, some strange indeed. Though I read it years ago, I find myself still mulling over certain stories.
For Children ... and All of Us
Many children's stories have allegorical elements. Here are two that are purely, wonderfully allegorical.
In these two fully illustrated books by R.C. Sproul, a grandfather tells stories to his grandchildren that impart beautiful truths in a magical way.
Fantastical Fiction Seasoned with Allegory
These works are not allegories in the true sense. But many of them have bright flashes of allegorical elements that will delight. (For example, when Jill tells the lion, Aslan, that she is dying of thirst, but she will need to find another stream to drink from because He, a great lion, is between her and the stream, Aslan replies, "There is no other stream.") Whether or not they contain any allegorical elements, they all point to deeper truth beneath the surface of the story that will make you think, break your heart, and heal it again.
Works by C.S. Lewis:
The Chronicles of Narnia
No matter your age, if you have not read the Chronicles of Narnia, read them. I was twenty-one when I first read them, and I still weep, worship, and leave with a fuller heart each time I revisit the land of talking beasts. There are 7 volumes. You can read them in the order in which they were published, as I did and recommend (beginning with The Lion, the Witch, and the Wardrobe), or in the order they take place chronologically (beginning with The Magician's Nephew). Regardless of the order in which you read them, be sure to read them all, concluding with The Last Battle. I cannot point to any book, besides God's word itself, that fills me with more hope than that little book.
The Chronicles of Narnia (7 volumes) – also available for sale individually, in a number of different editions. The movies, while good, are NO SUBSTITUTE for the books!
The Great Divorce
A dreamlike bus ride from the suburbs of hell to the outskirts of Heaven, this tiny book reveals the human heart like a scalpel in a surgeon's hand, while wrapped in an intriguing fantasy adventure. Divorce yourself of any notions that this book has anything to do with a marriage gone bad. Rather the title comes as a rebuttal to The Marriage of Heaven and Hell by English poet William Blake. With apologies to Lewis, I'd say you can disregard the title and just revel in the story.
The Screwtape Letters
Here we get to read the witty, bureaucratic yet terrifying letters of a senior demon, Screwtape, to his nephew and more junior demon, Wormwood. Their correspondence all centers on "the patient" – an ordinary human like us, who Wormwood is endeavoring to keep out of the grace of God and bring to ruin. Chapter by chapter, we follow the patient's progress as we gain insight into some of the pitfalls that our unseen enemy lays in our path. Not an allegory but chock full of the same kind of spiritual imagination.
The Space Trilogy
It's intriguing to see the themes that occupied C.S. Lewis' thoughts manifest in different ways across his writing – from theology to children's literature to poems, and in this case, science fiction. Don't let some of the inaccurate imaginings of space bother you. The books were written well before we had put a man in space; today an author would only need to shift the action to another galaxy or parallel universe, rather than a nearby planet, and the particulars would work fine. The first book, Out of the Silent Planet, is a grand adventure and easy read that keeps you on the edge of your seat. A strong middle school reader could enjoy it as well as an adult. The second volume, Perelandra, delves deeper into theology and, although not an allegory at all, the sense of discovery and underlying truth it contains lights my soul in the same way. That Hideous Strength, the conclusion to the trilogy, is tough sledding for the first portion, which takes place on Earth and involves a lot of political machinations in British academia. But for the reader who keeps going, there is a purpose to it all and an utterly glorious ending. The first book can be read alone without leaving the reader hanging.
The Space Trilogy 3 volume set (also available for sale individually)
The Green Ember Series
by S.D. Smith
Like the Chronicles of Narnia, this was written for children, but there is nothing childish about it. I found myself quickly immersed in a world populated by rabbits (with swords!), who dream, fight, and die for one another and the hope of the "Mended Wood." While not an allegory, a discerning reader will find it impossible to miss certain allegorical elements like the great new-creation hope for a mending of the world and the advent of an age of peace for rabbit-kind. I dare you to read passages like this without your heart being stirred: A young scribe says to her elders, "We had no idea that when you gave us all the light you did, you were guiding us to one day strike out at the darkness so fiercely. We have ... made a hard dart at the darkness. We have seen cracks forming and light seeping in."
It's also just a rollicking good adventure!
The four-volume series and several related novellas are available at: https://sdsmith.com/store/
The Circle series
by Ted Dekker
This high-adrenaline series is part fantasy sci-fi adventure, part allegory. It follows the adventures of Thomas Hunter, a man from our own world who finds himself translated into an utterly different, beautiful and dangerous reality whenever he falls asleep – and back to our reality when he falls asleep in that world. Fuse Magazine calls it a mythical epic, saying, "Put simply: it’s a brilliant, dangerous idea. And we need more dangerous ideas." The four volumes are Black, White, Red, and Green. (Emphatically not for children – these deal with heavy topics and can be quite violent in places.)
The Circle series Vol 1-3 (Green sold separately, and all books may be purchased individually.)
The Wingfeather Saga
by Andrew Peterson
Not pure allegory, but a beautiful allegorical thread ties the narrative together and blazes into view in the final book of the four-volume series. The fantasy adventure series is written for children, and makes a great read-aloud, while captivating adults (at least adults like me). The Igiby children live with their mother and grandfather in a not-very-nice world, which seems to keep getting worse as they discover who they are and what happened to their father. The first book, On the Edge of the Dark Sea of Darkness, is a lark, peppered with hilariously ridiculous footnotes and passages of silliness worthy of the title. They get progressively more serious as the series unfolds.
The series is available at https://www.andrew-peterson.com/the-wingfeather-saga as well as other bookselling sites.
For Writers and Lovers of Writing
The Writing and Reading of Allegory
essay by Dorothy Sayers
Famous for her Lord Peter Whimsey detective novels, Dorothy Sayers was a formidable thinker, a contemporary and friend of C.S. Lewis. She wrote a number of essays on the arts and Christian thought. I found her examination of allegory very helpful. It is part of her collection of essays called The Whimsical Christian, which may only be available in a second-hand edition.